Bridging Gaps, Scaling Success: How Shift Academy's Evan Klein & Hector Hernandez Empower Frontline Managers

Hector Hernandez
It's knowing how to really understand people. You gotta take a lot of leaps of faith, know the audience that you're trying to serve, and adapt to them to their needs.

Thomas Igeme
Welcome to another episode of our podcast, where we dive deep into the world of leadership, enablement, and entrepreneurship. Today's episode promises to be a fascinating journey as we're joined by two exceptional guests, Hector Hernandez and Evan Klein, who are reshaping the landscape of managerial development and coaching with their groundbreaking work at shift academy. Now, when I think about reshaping landscapes in big ways, I think about two people who ultimately were the inspiration behind my family name, Luai and Lume. Now, once upon a time, long ago, but not too long, in a bustling village nestled between rolling hills, there were two master craftsmen named Luai and Lume. Loi was renowned for his exceptional skills in building strong, reliable bridges, while Lume was celebrated for his expertise in designing advanced water systems that kept the village flourishing.

Now, despite their individual talents, the village faced a growing problem. The old bridge over the river was crumbling, and the water system was struggling to supply enough water to the expanding population. The village council realized that the solution lay in a unique collaboration between Luai and Lume. Luai would construct a new, robust bridge to withstand the test of time, and Lume would design an innovative water channel integrated into the bridge to efficiently manage the village's water supply. And so, together, they embark on this ambitious project.

Ultimately, thanks to Luai, you end up with a bridge that is sturdy and capable of supporting the heaviest loads and withstanding the strongest floods, while Lume's ingenuity brings forth a water channel that not only provides a steady water supply, but also prevents flooding by controlling the river's flow. And so, through their combined efforts, you have this new structure that is critical for both transportation and resource management, and you take what was once the blight of the village and turn it into the source of their prosperity. And like Loi and Lume, the successful collaboration between Hector and Evan has truly transformed what is possible for many of the organizations that they work with. They formed shift academy in order to address a persistent problem. Despite frontline managers being vital for success, many, if not most, fall short in skills to lead teams and businesses.

And the reason is simple. Managerial development often gets sidelined. Companies primarily focus on individual contributors and their senior leaders. And in that awkward gap that exists with very little investment, their lack of impact shows they created shift academy in order to help their clients solve this challenge at scale rather than traditional, often ineffective, training programs. Evan and Hector are focused on real world observation, feedback and coaching.

By leveraging recorded coaching calls and data, they offer actionable insights tailored to each manager's unique needs. They also introduced peer to peer development pods to encourage skill building, collaboration and connection. In our conversation today, we'll explore a variety of topics, starting with the influences that shaped Hector and Evans entrepreneurial journeys. Hector will share how his frequent relocations as a child instilled a comfort with uncertainty, a crucial trait for any entrepreneur. Whereas Evan will reflect on his family's entrepreneurial background and how it influenced his approach to risk, we're going to delve into their individual paths to leadership, the formation of shift academy, and their unique coaching methodology.

You'll get to hear about the early influences that shaped their leadership, leadership styles and the importance of empowering leadership, a concept that stood out to Evan during his time at LinkedIn. Our discussion will cover emerging trends in b two B sales, the balance between expertise and energy in leadership, and the role of AI in sales enablement. Hector and Evan are going to share their insights on the necessity of individualization in coaching and training, the impact of diversity and inclusion in sales training, and the future of manager development. So sit back, relax and get ready to be inspired by the, the incredible journey of Hector Hernandez and Evan Klein. Let's dive into the conversation.

Evan Klein
You know, before we get into kind of the work stuff of things, I'd love to go back to the beginning and kind of dig into a little bit of your childhoods. And in particular, I'm curious, you're both entrepreneurs now. Can you pinpoint any moments in your childhood that you think hinted at your entrepreneurial future? So growing up, I moved around a lot. Like, by the time I was in high school, I had already been like at twelve different schools, two different countries, like tons of different states.

Hector Hernandez
Like, I was very used to being the new kid. A couple of years ago, I was at my parents house and I picked up my old high school senior yearbook and like, I just was reading through the comments took me by surprise because there was like more than once, like a couple of people said some variation of like Hector, you're super comfortable in your own skin. Like, ah, you're marching to the beat of your own drummer. That's really cool. It's funny because I remember being in high school and not feeling comfortable in my skin at all.

I don't have a story about, oh, I started a lemonade stand or I did this. It's actually what I realized is that growing up, because I moved around so much, I became very comfortable with, like, uncertainty and newness and adapting to different situations and not having, like, a very stable, if you will, environment, which I think that was my competitive advantage. If I could advice the parents is, like, move your kids around. Maybe not places to places, but pull the rug from under them a little bit, because it teaches you how to handle uncertainty and being new and the unknown and being comfortable with the uncomfortable, even if at the time, you're not consciously aware that you are quite comfortable being uncomfortable. I think that prepared me more than anything else for entrepreneurship, because you don't have that stable path.

You don't have, hey, I put in my 40 hours. Here's the promotion track, and here's my salary, and every two weeks, this is what's taken out for insurance, et cetera, et cetera, et cetera. You got to figure it out. You got to take a lot of leaps of faith, but you do be somewhat subconsciously comfortable with that discomfort. What about for you, Evan?

Evan Klein
My answer is almost the opposite. I've always. I became an entrepreneur, like an official own my own, do my own thing entrepreneur, like, I would say relatively mid career. Right. This is somewhat new.

I've always had the kind of, like, the DNA to be an entrepreneur in that, like, I'm creative. Plus, it's that kind of combo, being creative and strategic and, like, love finding, you know, kind of exploring why things are done the way they are and finding better ways to do things, whether that be a product or whatever. And I could, you know, lots of examples of that when I was a kid and monetizing that, by the way, into a business, it was always fascinating to me. But I think I never really became an entrepreneur officially until relatively late, because I was not comfortable with the uncomfortable, and I did not embrace that. The risk part of being an entrepreneur was very scary to me.

It was kind of like balancing those two things where in my head, I wanted to be an entrepreneur, but in terms of actually making the leap and becoming one, that was very difficult. And the reason for that is because I actually come from an entrepreneurial family. Parents owned a couple shoe stores. I loved that. I think that was cool.

But there was always this thing in the air of, like, the other shoe could, you know, potentially drop. And that was stressful on the family of, like, this isn't, like, a steady corporate job where you work for 30 years and, like, it's a pretty guaranteed level of security. We never had that. And I think that that lack of security made me less comfortable with the. Of.

With being uncomfortable and with, like, jump, making that leap, and that shapes me as well. And when you think of Hector and I working together, I think, like, those patterns of me being the more probably risk averse one. We embrace those differences, and I think that those are positive for our partnership. Evan, I'm curious who some of your earliest influences were and how they've shaped your approach, maybe to leadership in general or entrepreneurship particularly. Leadership, for sure, is an easier one for me to answer.

I was blessed to have some just amazing leaders in the right infrastructure. So I'm talking being at LinkedIn for a long time, I think the most formidable years of my career at LinkedIn and a couple leaders that stuck out to me, Lauren Johnson, Sean Walsh, Ben Putterman. They come to mind because they fostered an environment where it was leading based on empowerment versus leadership of the anti empowerment, which is kind of like the detractor or diminisher qualities, which I'd had a lot of leaders, you know, and managers and bosses in my career who would have been just very diminishing. And I would say if I had been a leader myself under them, I probably would have had those same diminishing tendencies, because I just wouldn't have known any better. It was, you know, people like Lauren, Sean, Ben, who showed me, oh, my God, there's a much better way.

It manifested where I could then emulate that when I was able to become a leader. And the reflection there is, it's kind of like the viral nature of how leaders show up not only has an immediate impact, but then could have an ongoing impact as well. Could you make it real for us with, like, an example? What is empowering versus disempowering leadership? I'd say the headline is knowing the right buttons to push with someone in a way that kind of allows them to be their best selves.

There's no recipe for that, because every individual is so different. But I can share what that looked like for me. And what comes to mind immediately is. So I was talking about when Lauren Johnson was a manager of mine, when I was an actual frontline seller at LinkedIn, and it was relatively early in my career. And I'd say that what he knew about me is that I would feel the downs of a life as a seller, being behind, not getting a deal, worrying about where I was way more than I would feel the ups when things were going really, really well.

He knew that about me. I would say I also had this idea of maybe glass half empty, somewhat neurotic point of view, and that meant that when I would give my forecasts, it was usually lower than where I would actually end up for a year, a quarter, etcetera. And that wasn't because I was trying to like game the system or as they say, sandbag. It was because like, again, that kind of neurotic nature in me was just like, oh well, there is going to be something that doesnt go my way. And so let me be more pessimistic, Lauren.

When he would forecast, and I didnt learn this until after, by the way, when he would then take my forecast up to his bosses for the broader aggregated forecast, he would bump up whatever number I gave him by something like 2020, 5% because he knew thats where I would end up. But he wouldnt tell me that because he knew if I knew that he did that it would actually increase the amount of pressure on me and almost reinforce that neurotic nature that I had. He was like, hey, this guy's performing and I can actually empower him to be his best self in this kind of unique strategy. Now that is kind of a one off example, but it was very life changing and it worked. It worked really, really well.

Hector, I love to hear from you. What do you think of as your area of expertise? Think it's understanding people. You can call that leadership. You can use the coachy language of like on walking your potential and stuff like that.

Hector Hernandez
But what I'm very, very good at is understanding the clients that I work with directly, one to one, as their coach to help them figure out what they need to figure out and move in that direction. I think I am an expert in understanding what people need from their leaders to be able to be unlocked and translate that into coaching, translate that into training. By the same token, the ability to understand what people just generally need to progress, to get better observation of them in action, breaking their limiting beliefs, understanding how their brain actually clicks and works. And that's something bringing in even into, like, my class, I don't understand freshmen, but I know I don't understand them. So rather than try to talk down to them, which I know a lot of professors do, and just like, here's the textbook follow, I'm like, I want you to learn.

I don't want you to get a pluses on quizzes. And I understand you're here to just be exposed to stuff and be little sponges. So I'm going to be here. I'm going to serve you. It's knowing how to really understand people.

And that journey too, by the way, because I'm like, oh, I'm an expert. I'm like, I'm not an expert. That's where I get a lot of energy, and that's where I get, like, really jazzed when I'm talking to someone. I'm trying to figure out, like, what makes this person tick. And when you do, well, you have the Laurent's.

You have leaders that actually know, like, Evan needs this. I could tell Evan all the platitudes to make him feel good or whatever he needs, et cetera, et cetera. Or I could play into whatever he knew. Evan was able to use that to get the most out of it. Could you tell me a little bit more about what you think of as the difference between kind of those two approaches or energies to kind of work, like, leaning on expertise versus leaning on energy?

What is the ancient saying? The wise person is the person that knows. They know nothing at all. So, like, yes, to your point, like, I can sell myself as an expert. I have a ton of knowledge I've accumulated in all these different areas.

Hours of practice, et cetera, et cetera, et cetera. But that's the thing, is that the more I've learned, the more I've dove into these topics of leadership and people and what unlocks them. The more you read, the more you read Daniel Kahneman's work, for example, and you realize, like, oh, man, yes, I know nothing. And I actually should embrace that. And the whole expertise is not if we say expert, we think, like, there's a.

There's a roof, and you've hit that roof. You're now an expert, a true expert. You're finding energy to always be growing and always be learning and always be adapting. And the more you learn, the more you grow, the more you realize, like, wow, I know nothing. And you keep going.

You keep going. You keep going. So I am at a point now where I'm very comfortable monetizing what I've learned, very comfortable going toe to toe with anyone in a conversation about these things. But always with that point. Like, yes, it's.

It's confidence, but it's all humility, because I learned, and I could be completely wrong about this, and that's okay. There's expertise that, through hours of practice and experience, you have earned the right to share your perspective. Any true expert in any area, they will be the first to tell you, like, oh, hi, I know nothing, and I am still trying, and I'm learning, and I'll share what I've learned, but what I now may not be true tomorrow. The way that this makes sense in my mind, because I agree with everything you just said. The expertise points you in the right direction of where to focus that energy and kind of gives you that grounding on.

Evan Klein
If you think, by definition, to actually make a massive impact, you're on the outer edges of doing work and offering something that hasn't been offered before in that way. That means that expertise only takes you so far because your expertise is based on things that have already been done versus what things could be done. And that's where the energy comes in, right? Like, the actual value doesn't come in. Like, hey, I've done and seen this a million times.

I'm going to share that with the world. It's. I've seen enough, and I'm going to sit here with that energy and pontificate this and think and think and think about what it could be. And that's where differentiation value, the magic really happens. What was the catalyst for working together at shift academy?

You guys were both at LinkedIn. What was the moment where you were like, we think we want to do this thing, and we think we want to do it together? We did not work together at LinkedIn. We worked in sales enablement at the same time, part of the same family. But I don't think Evan and I ever once collaborated on a project.

Hector Hernandez
I think the one thing was, like, once he needed people to help run some sims in New York, and I was in New York and I showed up and he told me what to do. I'm like, yeah, great. This looks great, man. Awesome. Always a ton of, like, respect, but, like, I had been in the space of.

I got a head start with entrepreneurship. I had already been on my own solo, doing executive coaching and contractual facilitation for hire HH learning for a while. Coaching had always been something that I was obviously interested in because I did, but also something that the more that I worked as a coach, and I worked through different organizations as a coach, and I was contracted by content creators to deliver the content around coaching, the more I was frustrated with what was out there at the time, I couldnt exactly put my finger on what it was. Now I can say it was like. It was just so generic.

It was not specific to the roles and the functions. It was so rigid. It was just off the shelf. It was designed to actually not go deep and where people needed to go deep to do their jobs functionally, et cetera, et cetera, et cetera. Going to put my finger on it.

One of the great things about working at LinkedIn was that you are exposed to this exceptional network of really, really, really great people. Stayed in touch with all of them. And Thomas, I know you do the same. Evan course, does the same. And one of these people was the wonderful Al Smith.

He's over a HubSpot. He's exceptional. Human to the bone. Love the guy. I worked with him closely on the global programs team.

But long story short, we'd be just catching up in general, and he'd be like, Hector, what are you thinking about? What are you working on right now? Like, coaching? I'm trying to unlock this. Blah, blah, blah, blah.

He's like, you know, you should talk to Evan Klein. I talked to him the other day, and he's thinking about some interesting things. Like, you guys should talk. Yeah. And thought about Evan, honestly, at that moment, like, oh, who?

To reach out this. Because there was nothing there, there, there. But then Evan and I talked, and I remember that first conversation, like, the call ended. I'm like, there's something here. And it was like, one of those calls, you're just, like, kind of dancing around something, like, trying to figure out how to dance together or whether they're just dancing around.

And I'm like, that was a good conversation. Finally, we just came to the point, like, hey, do we have something? And, you know, maybe we. And we pursued our first client with almost this agreement that, like, listen, if nothing happens, and in six months, fold our cards, shake hands, go play another game at the casino. But it started to work, and it started to work, and momentum started to build.

And here we are a year, I think only a year later, by the way, man, we might be on our anniversary. Probably should have, like, cemented, literally not the LinkedIn anniversary, but when we actually. Yeah, you're supposed to. We send each other flowers or something. Flowers, bottle of champagne, roses.

Evan Klein
What's your side of that story? When we talked about those first, let's say, three or four meetings, Hector, I think you were talking a lot about the synergy of the what, meaning what gap in the marketplace we both felt and agreed on could uniquely do together. So I think that was a big part, but that was only maybe half the equation. We also pressure tested what we wanted out of a business, so there was similarity in terms of what the business was going to be, and we had a ton of great synergy there. But it was also like, what do we want out of a business in the first place?

And the overlap there was perfect. What I mean by that is things like, we wanted a lifestyle business that allowed us to put our families and work life harmony first over putting a, hey, let's put our heads down for five years and IPO, something with venture capital that was not even on our radar. Neither of us wanted that. So we were very similar in both what we could do and how we want to do it. That to me, like, I'd almost say the latter is more important when finding a partner than the first because the first, like what you're going to do is going to evolve anyway.

But like, what you want out of this if you're not completely on the same page, there is where partnerships go wrong.

You know, one of the things that really differentiates what you do guys do at shift academy is this deep focus on observation. What are some of the big emerging themes around the world of b two B sales? It's this just new push for rigor in these businesses. In terms of prior to 2022, 2021, there was a lot less drive for margin. It was growth, growth, growth that meant that just this relentless need for operational excellence, Rigor, whatever you want to call it, it just wasn't as emphasized.

And then there was this relatively abrupt shift where that wasn't the case anymore. And what, at least in public organizations, but I think private follow the same path is just like, hey, we need to deliver results, we need to grow, but we need to grow smart, we need to grow at a high margin. And thus we need to just demand additional layer of rigor from a sales perspective. And that shift is, you know, has just a huge impact on process, on culture. And so I think companies are still, whether they know it or not, struggling to make that shift.

You know, the companies that are doing that well are retaining their people, growing their people and thriving. And I think other companies are struggling to do that and they're seeing massive attrition. That's the biggest trend that I would identify. It's rigor because before we used to say do more with less, but we're almost coming to the point like, no, now you need to do more with nothing. Like nothing else.

Hector Hernandez
Like you really need the operationalize excellence and you need to be able to make it work and click. I think now there's a big realization that for a lot of times in enablement and sales, like the approach of like, oh, you have these big ubiquitous methodologies, challenger works for all, blah blah, blah blah, work for all. Is this need for individualization. Like everyone is in different places, literally. Some work from home, some work from the office.

Like, we are a completely different place. The world is changing every day. So that requires a much deeper level of customization, but at scale, which is the problem that everyone's trying to figure out right now. I'm realizing that we need to maybe stop looking at the big companies for innovation, because historically they're like, all right, name your big company. What's Facebook doing?

Let's learn from Facebook. I find that when we talk to small or medium sized organizations, they are so much more open to innovative ideas and they're already halfway there. They were almost just like saying, yes, yes, yes, and let's do this. When we talk to a lot of the bigger organizations, their minds are actually stuck in 20 202-021-2022 and it makes sense. You're bigger risk averse, you have shareholders, you more to answer to.

But I think it's a time for everyone to shift away from learning from the big giants and look at the smaller companies. They are open and willing and trying really, really cool things. When you are walking into a company and kind of getting a sense of the degree of operational rigor that they have, what are some of the things you're looking for? Let's talk in context of sales, because that was a lot of where my focus was on when I made that comment initially. It's going to be things like, is there a defined sales process?

Evan Klein
That doesn't mean a one pager sitting in the archives of the organization. That is the sales process. I mean, like, is it entrenched in the plumbing of the business? Are there exit criteria? Do those exit criteria get input into CRM?

Does that funnel up to their forecasting calls and their forecasting methodology? It's really that a baked into the business form of accountability through to coaching, through to a recipe for success that if you do these things, you will be successful in your role as a sales rep at this organization. And having that codified to me is that now I think there's a lot of organizations who don't have those things codified yet want to appear, still say we value rigor or we value operational excellence, and yet they don't necessarily see the result. Its more just tough talk from above. And then they wonder why its not working.

But the companies that youre seeing that are doing this really, really well, ill call one out. 6th sense does this exceptionally well. 6th sense is a company we work with and blown away at how much rigor that theyve built into their system and how well they operate that thats how I see it. Theres nothing more I can add going that level deeper. Everyone agrees we should have a process and we encounter a lot of companies like what is your process success specifically?

Hector Hernandez
And just go deeper in terms of like how that process can be utilized so effectively. So our approach is we have a coaching framework, but our coaching framework only works in context of the organizational goals and what they're trying to drive. If we show an organization and they don't have real specific process or rigor around how what they are trying to apply and drive, our coaching can't go as deep as it can with an organization like 6th sense was like, oh, early deal stage, coach, early deal stages. These are the criteria. This is the literal list of ten things that we look for that we pressure test.

Can you coach to that? Absolutely. Because now we can design a manager enablement program, a coaching program that isn't just build trust, hug the person and ask questions. It's like, no, no, no. We are driving through our trust, information about these ten specific things and tactical, tangible, specific outcomes, next steps, et cetera.

Evan Klein
What is that mix between the kind of very meticulous accountability around behavior and the quote unquote softer trust and openness and vulnerability, kind of like required for change. How do you guys think about marrying those? Do you tend to focus on the rigor and be like, the trust will take care of itself? What is it? Like the soft, and I put that in quotes, part of coaching fit into the shift academy process or viewpoint.

Hector Hernandez
I mean, trust is fundamental, but trust is not being nice. Like think about it in the context of a parent. Like, my job as a parent is not for my child to like me, is not to coddle them, is not to shield them from the world, is for them to grow, for them to thrive, for them to be a good human. And that requires holding them accountable when they're going down a path to celebrate, when they're doing things well. And yet, as a parent, like, you're able to build that instant trust instinctually.

But it's not that different. As a leader with the people on your team, your job is to help them thrive, create the conditions for them to succeed, to move them, to push their boundaries for them to grow. Grow trust is essential, but so is accountability. Because if I'm just nice to you and I make you feel good, but I don't help you do your job, I don't help you grow, I don't help you follow through in your commitment, I'm failing you that. And I think it's also like, what are you trying to coach too?

Evan Klein
And being very mindful of that? Because when you think of operational excellence, rigor et cetera. For a sales organization, it's oftentimes coaching to the day to day behaviors that lead to success. So oftentimes defined by a dashboard, how much pipeline, how much activity, what's the success rate in moving something from stage two to stage three? And I think that that is where it might feel a little bit more, hey, that isn't focusing on the behaviors as much, but the outcomes and ensuring they hit those outcomes.

But then if you're coaching to skill, which are, how do you actually do those things? Which is a nuance, but it's a different kind of coaching, then it's like, hey, let's go really deep to ensure that you are elevating the skills required to reach certain outcomes. It feels very different, and I think that's where there's a lot more openness to helping, where the coaching should be anchored on not, this is how you do it and more of an empowering, hey, let's co create what that looks like and how you coach e and your unique strengths, personality gaps, et cetera, how you can do that. I'm curious about what you both have. Learned in the journey of shift academy.

And specifically, have you encountered any findings that contradicted your previous beliefs about sales enablement, coaching, or training? And if so, could you share an example? Don't know that I can share a specific example because there's so much that I'm learning and unlearning and things that are being validated and revalidated every single day. What Evan and I have done well in partnership and through our business is that, like, one of our core operating principles is this idea of we adapt to our clients and we adapt to the situation. So we are not off the shelf.

Hector Hernandez
We are not the holders of the great sales coaching framework. We have an approach, but it only works if we can rejigger it a little bit in the context of each client. So it's one of those things that we kind of try not to walk in with this mindset of like, oh, I know what's right. Oh, this problem. I know exactly how to fix this.

Like, this is just validating my beliefs and stuff like that. We try to walk in with more of a, we need to understand each client in things we've seen and trends like, sure, we can pull on, but if anything else, I think it's more validated. The assumptions I had about salespeople are innately just hungry people that really do are curious and want to learn and want to be better. And, yeah, they want it fast. No patience for a floppy coaching training back in validated time and time at Cayenne.

But I think those are good things to just remind ourselves, like right know the audience that you're trying to serve and adapt to them to their needs. I think I agree. I mean, the way that it makes sense in my brain is when we look at the definition of best practices. I think one of our initial hypotheses is that those best practices would be, let's say something like 60% consistent across all organizations and then 40% would really need to fit in that organization. And I think we're now probably at 80, 515 or 90 ten where the customization is a huge element of what we do and is really important.

Evan Klein
But I don't think what's being customized is the how to do things. We're actually quite blown away at how consistent those best practices manifest across all organizations. Different role types, different levels of experience. It's the language, it's the maybe even the sophistication that needs to be customized. And I'd say that we, that is a big finding, that surprisingly large ramifications on our ability to work with customers and scale.

I mean, I think that's actually been a good learning. And being like, hey, we know what good looks like and that good can apply to a lot of different situations and we can make it feel like it. We can really work with a customer to embed it into the language and their culture, but we feel good about what good looks like. Do you guys have an example of kind of a known good that you found is more applicable than most people realize? A big learning that we thought would be specific only to sales.

Is this idea of like questions in when you're doing deal coaching with a rep sales rep, we have a best practice, which is how do you scale that? You're focusing on one deal. Now, of course you're usually working with a sales rep that might have a portfolio at any given time, or maybe it's 50 deals that they're working on at any given time, or 50 accounts. But if you are going deep into one deal, there's an opportunity to scale those learnings to other deals. It's like if there's this opportunity with this deal, it may be an opportunity to be very specific.

Might be something like, I'm only speaking to too few potential decision makers. I need to broaden my multi threading, my relationship building across the account. If I really want to drive consensus and be successful, very common one, then if you could say, great, if that's the case in this one deal we're talking about at this moment. Hey, let's take a step back. What other ones of your accounts or deals is that also applicable to?

And then it's like, okay, let's think about some things that you can do to scale, what you would do for this one account to all those accounts, and boom, you get a lot more value. So that as an idea, transcends just the sales outcome. Because if you are, if you're talking to someone who's in a completely different function outside of sales, but let's say has one particular project they're working on, you could go deep into that project and diagnose, hey, we found some gaps or some areas of opportunity within this project. Well, hey, take a step back. What other projects that you have that you're working on right now that those same gaps might apply to?

And what can we think about at scale to mitigate those gaps across all those projects versus just that one project? So it's things like that, the same ideas apply. What are some of the lessons that you think you picked up from your time in big tech, and what are some of the things that you think you've had to unlearn? There's so much goodness, right when you work at a big organization of what you can actually see. I will say we were lucky to work at LinkedIn, where you got a good degree of autonomy in a lot of moments and instances to be entrepreneurial in terms of your approach.

Hector Hernandez
And first and foremost, like, unlock this idea of entrepreneur as a job. It's a mindset. You can be incredibly entrepreneurial and be a entrepreneur in a corporate environment. It just sucks. You have to redefine what that actually means, et cetera.

One thing, though, I will, I definitely took away is this idea of scaling and scaling your idea. And it's a big word, it's a buzzy word. But when I went into my own practice as a coach, I realized very quickly that if you can't scale, you can't sell it. Otherwise, literally, pragmatically, practically, you are the product that you are one on one with person, and that takes a lot of time. And if you're trying to offer yourself into larger organizations, and I don't mean like a thousand person, like a 250 person organization, you need to be able to scale and always thinking of that, not letting that be a ball and chain that weighs your decisions, but something that you're constantly thinking about, like, if I am going to grow as an entrepreneur, if I'm going to serve larger and larger and larger and larger clients.

I need to really understand the value of scale and think of my solutions in terms of scales. Otherwise, you won't be able to sell yourself, you won't be able to sell your product, and you won't be able to manage the work yourself. To me, the number one thing that I learned to do in a corporate environment was sell. And im going to be specific, of course, in enablement. My job ultimately became how to teach how to sell.

Evan Klein
But in doing that, I had its almost like youre on the cutting edge of really understanding the best practices of sales and the amount that weve been able to apply that. Because, look, as an entrepreneur, ill tell you, your number one job is sales. It just is in every capacity. One of the projects, I'm not going to speak to a specific project. One of the things that during a part in my career in enablement was basically owning the project for thinking about the go to market sales narrative, going really, really deep about how the sellers at LinkedIn would pitch, you talk about the value and the problem they were solving.

I went down that whole PEB Challenger methodology approach to building that narrative. And the lessons I learned on doing that, we applied. One of the first things Hector and I did was we built a narrative, kind of a two page infographic front and back that told what the problem we were trying to solve, our unique approach to selling it in a really cohesive way, the amount of time we spent on that. But that allowed us to tell the story, not only for us to tell the story, but tell the story in a compelling way. That also allowed, when we're talking to a client, we're talking to someone like a Nikki at $0.06.

It also allowed for repeatability for Nikki then to go advocate for what we were doing by telling the story again. I never would have learned that if I, without the exposure I had at big corporate. If you think about it, the converse of that is, what do we have to unlearn? I think the easiest way for me to answer that is I do agree. I think that when you're in a big corporation, I always felt that LinkedIn especially, I had a huge opportunity to scratch an entrepreneurial itch.

What got in the way of that was when youre looking after such a big portfolio of theme and stuff and projects that you no longer have the ability to focus deep enough in any given one thing that allows you to be entrepreneurial by nature, youre surface level on too much. What I think were unlearning is this. We you know, it's always tempting, you know, you to try to do a lot of different things as an entrepreneur. You do more things and there's more potential customers and more needs you can attach yourself to, but then all of a sudden you lose the value, I think, and it erodes. And I lived that firsthand.

And that's why kind of like one of the operating principles that Hector and I aligned with at the very beginning is this just importance of focus, focus. What are the biggest changes or innovations that you see happening in the world of sales enablement over the next decade? Listen, I don't, I don't want to jump on the bandwagon AI, but AI is, is a, is a real thing. And I am actually currently I'm going to start work with two senior sales leaders. The problem to be solved of what we're working through is literally AI is at risk of replacing their entire sales.

Hector Hernandez
They are in a transactional business, even they will admit, like, listen, I, yeah, people can go online and there can be a bot and they can be started. It's a real thing saying that like all sales people are going to be replaced. Absolutely not. But how we actually use AI, how leverage it to be productive, how we leverage it to solve certain efficiencies, but then marry that with the people, human element of Siem. And as you think about that, the role of managers is going to be even more essential.

Really understanding how do you manage the people and whatever anxiety around the change of the role is coming and managing these technologies. And also the idea of now change. If you think about more senior level leaders constantly having to drive priorities, constantly having to drive change in normal times, air quotes like before the year 2022, you probably a couple months, maybe a year or two between cycles of massive change. Those cycles, massive change of reshifting of priorities is now going to be quarterly, quarterly, quarterly, monthly, monthly, monthly, more exponentially faster. So for sales organization, in sales enablement in general, really being able to help salespeople, sales leaders navigate that shift towards AI, equip them to still be incredibly invaluable to the organization, but still use the technology that's here.

And specifically for leaders, for sales enablement to be ahead of the curve and see, say change is coming, shaping of priorities, communication of priorities is changing. Constantly helping leaders to be able to drive those things, because otherwise they're on their own. And if sales enablement is just focused on rolling out a methodology, you see the bigger picture of what people will need. AI is the catalyst. It's the big thing.

Evan Klein
But I think we can be more specific here. And that is AI is going to allow sales organizations to capture new data and specifically behavioral data. When you think of enabling someone, the idea was always, hey, we could give them best practices. Then their job is to apply those best practices in their day to day. And then we get some data from what they're doing in that day to day, how they're applying those behaviors, CRM, are they inputting things?

But there was a lot missing. When you're interacting with a customer, it's a complex thing. How do you ascribe data to that in really be able to use data to optimize those kinds of rec customer interactions? Now with tools like Coors and gong and AI, it's going to allow you to actually do just that, where you're able to glean from that interaction that's happening in the field and use that to optimize. I think that's going to fundamentally change the role of enablement.

It's going to allow enablement to get closer to the actual field. In a world where maybe enablement is using data to find big trends across the whole sales organization of gaps, they're not doing discovery well, we can. We know that because the aggregated stage two to stage three is lower than it should be, or pipelines don't, whatever it's now, hey, this specific rep, we have data that, hey, they have XYZ gap. And we know that in terms of not only the KPI's, but also the data that we're seeing from that AI is those signals. And even then, let's have some intervention for that specific rep who's struggling with that exact thing.

And even then, it's like not only that, this deal is at risk because the AI is triggering several risk factors within this specific deal. Let's go into an intervention that the rep can use for that specific deal, and automating that whole process is going to fundamentally change that job. Now, how fast that happens, it depends on how fast we're able to like really pull that behavioral data in an actionable way. How does D and I, if at all, show up in your training programs? We're not going into politics, but the politicization of diversity and inclusion in teams misses the whole point, which for me it's just a question.

Hector Hernandez
Of course there's a moral question that's unquestionable, but it's efficiency, it's effectiveness, it's outputs. You will find people with the same background that think the exact same way. Ask these five people to solve the problem, you're going to come up with the same answer. If you have people from different backgrounds, different experiences tackling the same problem, you're going to have five different answers. You're going to have the multipliers of those when they come together, and it opens up how you actually are an effective organization, an innovative organization, and it's no different with sales.

And I think when we think about how we communicate coaching, how we communicate driving people towards outcomes, it goes back to our core principle that it's not a one size fits all. And knowing what motivates them and asking them to reflect, not because coaching is a game of 20 question, but because for me as a coach and you as a coachee to come up with a good path forward, we need to create information. And that information is going to be unique to you and unique to your situation, to your context, and what you're comfortable with, what you're aware of, you're not aware of. Then we can land on some outcomes, land on some situations. And by the way, if I'm going to hold you accountable, some people, I could literally just be like, all right, I'm going to be tough cop.

You go with that. Great. Yeah. Micromanage me. Love it.

Other people, you need a different type of approach. You need to be able to understand what's going to motivate them. You need to inspire them to the action, not just drive that action for us, it's just almost obvious that for you to drive a successful team and to coach successful salespeople, you need to meet those people, those individuals, in the individual ways. And yeah, there's some practices that are almost universal. The trust, the reflection, the good accountability.

But each individual needs different, unique things. Evan, given that you are newest in this pairing to the entrepreneurial life, is there anything you wish you had known back in corporate that you understand now from this experience that you'd love to go back and share with yourself? Yes. I think the biggest learning is how much value there is when you can be nimble. I think I spent way too much time in corporate worrying about how work was perceived versus the actual impact and value that was going to result from that work.

Evan Klein
And I think that the systems in corporate are set up to do that. And I think that I probably, you know, it's like the lowest common denominator. I think I could have done more impactful work if I had had more faith in myself, in knowing that perceived competence from others would come when the work was as good as the work could be versus during the journey of the work, worrying too much about how it was perceived. I think if I twisted that, like, not only would I have been happier and more successful, I would have driven a lot more value for the organization. That's also just as true of setting up an environment as a leader.

Like, I was partially responsible for setting up an environment, and I think I could have done a better job setting up an environment where it was about the work itself, the impact of that work versus the perception of that work in any given moment. I've learned the beauty of the entrepreneurial life is that you start from a position of ownership when you make decisions versus, like, a position of obligation. And when you're structured corporate structure, you have an obligation to your team, to your leader who has an obligation. That's cascading. So a simple thing like, hey, should I have.

Hector Hernandez
Should I go have lunch or should I take this call? Your decision starts from the point of a sense of obligation versus ownership of in that moment. And that's just one example. But it becomes very hard to really achieve the idea of balance, work life balance and harmony in a corporate structure because your decisions will always be made starting point of obligation versus the starting point of ownership. And once you can really evaluate decision like, is this the best decision for me?

Is this the best decision for the company, for the work, for the relationship that I have? And that makes all the difference?

Thomas Igeme
And now it's time for spoken stories, our recurring segment where we hear from some of the people who are most impacted by the work of our guests. Today I got to talk to three people who are happy customers of shift academy, and I had one question. What did they believe was shift Academy's secret sauce? I talked to Shawn Preston Walsh, the vice president of revenue enablement at Stackadapt, and Mary Beth Coyne, a senior learning experience designer of revenue enablement at $0.06. Here's what each of them had to say.

Hector Hernandez
I love working with Evan and Nektor at shift Academy because they get it. They understand what I'm trying to accomplish, and they're out there actively trying to get me tangible results. They're not bsing me. They're not giving me fluffy. They understand what it's like to move the needle with managers, with coaching, so we can get the productivity that we need.

Mary Beth Coyne
Evan and Hector's secret sauce is definitely how infectious their enthusiasm for coaching is. They know from experience just how impactful arming frontline managers with the confidence to coach can be to an organization. And they are just so excited, so invested to get our team to that point, which is great for us as an organization, great for the individuals that they're working with as they grow as leaders. So we are just super, super appreciative for how Evan and Hector show up for our team.

Thomas Igeme
And that brings us to the end of today's episode. When I think about Evan and Hector's story, I'm truly impressed by what they've built and how quickly they've done it. But I much more impressed by the model for deep, enduring, productive partnership that they display. Here are people who are great, not because they're exactly the same, but because they have deep respect for their complimentary gifts, have a really clear shared vision on where they want to go, and are unafraid to iterate and adjust over time based on what they learn. We need so much more of that in the world.

And my hope for you, dear listener, this week, is that you get to enjoy that kind of partnership. It might be just for a moment, but I hope that it turns into a movement. I'll see you next time. As always, I'm Thomas.

Bridging Gaps, Scaling Success: How Shift Academy's Evan Klein & Hector Hernandez Empower Frontline Managers

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1: Introduction to Shift Academy

2: Personal Backgrounds

3: Shift Academy's Approach

4: Future of Managerial Training

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